Delete file from hard disk etc.?

Can iTunes do the following, and how?
1. When I ask a file to be deleted from the Library, is there some way of asking for the file to be deleted from the hard disk itself?
2. If the location of the file has changed, can iTunes update its library and delete the unfound files from its list?

Boot the computer in Windows Safe mode with network support (press F8 on the boot screen) as a test to see if that helps.
*http://www.bleepingcomputer.com/tutorials/how-to-start-windows-in-safe-mode/

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